Details of the Drug

General Information of Drug (ID: DMD157S)

Drug Name

Montelukast

Synonyms

Brondilat; Montair; Singular; Apxi toxin; MK 0476; Brondilat (TN); MK-0476; Montelukast (INN); Montelukast [INN:BAN]; Singulair (TN); Sodium 1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetate; {1-[({(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl}sulfanyl)methyl]cyclopropyl}acetic acid; (R-(E))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid; 1-((((1R)-1-(3-((1E)-2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid; 2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetic acid

Indication

Disease Entry	ICD 11	Status	REF
Allergic asthma	CA23.0	Approved	[1]
Allergic rhinitis	CA08.0	Approved	[1]
Asthma	CA23	Approved	[2]
Intrinsic asthma	N.A.	Approved	[1]
Coronavirus Disease 2019 (COVID-19)	1D6Y	Phase 2/3	[3]
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Therapeutic Class

Antiasthmatic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

586.2

Logarithm of the Partition Coefficient (xlogp)

7.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Bioavailability: 62% of drug becomes completely available to its intended biological destination(s) [5]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.68 mL/min/kg [6]
Elimination: 0.2% of drug is excreted from urine in the unchanged form [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 hours [6]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.28489 micromolar/kg/day [7]
Unbound Fraction: The unbound fraction of drug in plasma is 0.002% [6]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.15 L/kg [6]

Chemical Identifiers

Formula: C35H36ClNO3S
IUPAC Name: 2-[1-[[(1R)-1-[3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanylmethyl]cyclopropyl]acetic acid
Canonical SMILES: CC(C)(C1=CC=CC=C1CC[C@H](C2=CC=CC(=C2)/C=C/C3=NC4=C(C=CC(=C4)Cl)C=C3)SCC5(CC5)CC(=O)O)O
InChI: InChI=1S/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/b15-10+/t32-/m1/s1
InChIKey: UCHDWCPVSPXUMX-TZIWLTJVSA-N

Cross-matching ID

PubChem CID: 5281040
ChEBI ID: CHEBI:50730
CAS Number: 158966-92-8
DrugBank ID: DB00471
TTD ID: D00QET
VARIDT ID: DR00382
INTEDE ID: DR1111
ACDINA ID: D00445

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Leukotriene CysLT1 receptor (CYSLTR1)	TTGKOY9	CLTR1_HUMAN	Antagonist	[8]
HUMAN cysteinyl leukotriene receptor (CysLTR)	TTSB6CA	CLTR1_HUMAN ; CLTR2_HUMAN	Antagonist	[9]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic anion transporting polypeptide 2B1 (SLCO2B1)	DTPFTEQ	SO2B1_HUMAN	Substrate	[10]
Organic anion transporting polypeptide 1A2 (SLCO1A2)	DTE2B1D	SO1A2_HUMAN	Substrate	[11]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[12]
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[13]
Cytochrome P450 2A6 (CYP2A6)	DEJVYAZ	CP2A6_HUMAN	Substrate	[12]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[14]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Montelukast

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Disease	REF
Zafirlukast	DMHNQOG	Moderate	Decreased metabolism of Montelukast caused by Zafirlukast mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[15]
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Coadministration of a Drug Treating the Disease Different from Montelukast (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Nateglinide	DMLK2QH	Moderate	Decreased metabolism of Montelukast caused by Nateglinide mediated inhibition of CYP450 enzyme.	Acute diabete complication [5A2Y]	[15]
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Montelukast caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[16]
Mitotane	DMU1GX0	Moderate	Increased metabolism of Montelukast caused by Mitotane mediated induction of CYP450 enzyme.	Adrenal cancer [2D11]	[16]
Metronidazole	DMTIVEN	Moderate	Decreased metabolism of Montelukast caused by Metronidazole mediated inhibition of CYP450 enzyme.	Amoebiasis [1A36]	[15]
Voriconazole	DMAOL2S	Moderate	Decreased metabolism of Montelukast caused by Voriconazole mediated inhibition of CYP450 enzyme.	Aspergillosis [1F20]	[15]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Montelukast caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[16]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Montelukast caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[17]
Alpelisib	DMEXMYK	Moderate	Increased metabolism of Montelukast caused by Alpelisib mediated induction of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[18]
Tamoxifen	DMLB0EZ	Moderate	Decreased metabolism of Montelukast caused by Tamoxifen mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[15]
Toremifene	DMQYUWG	Moderate	Decreased metabolism of Montelukast caused by Toremifene mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[15]
Phenylbutazone	DMAYL0T	Moderate	Decreased metabolism of Montelukast caused by Phenylbutazone mediated inhibition of CYP450 enzyme.	Chronic pain [MG30]	[15]
Mifepristone	DMGZQEF	Moderate	Decreased metabolism of Montelukast caused by Mifepristone mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[19]
Lumacaftor	DMCLWDJ	Moderate	Increased metabolism of Montelukast caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[20]
Ivacaftor	DMZC1HS	Moderate	Decreased metabolism of Montelukast caused by Ivacaftor mediated inhibition of CYP450 enzyme.	Cystic fibrosis [CA25]	[15]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Montelukast caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[15]
Primidone	DM0WX6I	Moderate	Increased metabolism of Montelukast caused by Primidone mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Felbamate	DM1V5ZS	Moderate	Increased metabolism of Montelukast caused by Felbamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Oxcarbazepine	DM5PU6O	Moderate	Increased metabolism of Montelukast caused by Oxcarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Cenobamate	DM8KLU9	Moderate	Increased metabolism of Montelukast caused by Cenobamate mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Fosphenytoin	DMOX3LB	Moderate	Increased metabolism of Montelukast caused by Fosphenytoin mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Phenobarbital	DMXZOCG	Moderate	Increased metabolism of Montelukast caused by Phenobarbital mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Carbamazepine	DMZOLBI	Moderate	Increased metabolism of Montelukast caused by Carbamazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[16]
Tazemetostat	DMWP1BH	Moderate	Increased metabolism of Montelukast caused by Tazemetostat mediated induction of CYP450 enzyme.	Follicular lymphoma [2A80]	[16]
Miconazole	DMPMYE8	Moderate	Decreased metabolism of Montelukast caused by Miconazole mediated inhibition of CYP450 enzyme.	Fungal infection [1F29-1F2F]	[15]
Ripretinib	DM958QB	Moderate	Decreased metabolism of Montelukast caused by Ripretinib mediated inhibition of CYP450 enzyme.	Gastrointestinal stromal tumour [2B5B]	[15]
Sulfinpyrazone	DMEV954	Moderate	Decreased metabolism of Montelukast caused by Sulfinpyrazone mediated inhibition of CYP450 enzyme.	Gout [FA25]	[15]
Isoniazid	DM5JVS3	Moderate	Decreased metabolism of Montelukast caused by Isoniazid mediated inhibition of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[15]
Rifampin	DMA8J1G	Moderate	Increased metabolism of Montelukast caused by Rifampin mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[21]
Rifapentine	DMCHV4I	Moderate	Increased metabolism of Montelukast caused by Rifapentine mediated induction of CYP450 enzyme.	HIV-infected patients with tuberculosis [1B10-1B14]	[16]
Delavirdine	DM3NF5G	Moderate	Decreased metabolism of Montelukast caused by Delavirdine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[15]
Efavirenz	DMC0GSJ	Moderate	Decreased metabolism of Montelukast caused by Efavirenz mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[15]
Etravirine	DMGV8QU	Moderate	Decreased metabolism of Montelukast caused by Etravirine mediated inhibition of CYP450 enzyme.	Human immunodeficiency virus disease [1C60-1C62]	[15]
Gemfibrozil	DMD8Q3J	Moderate	Decreased metabolism of Montelukast caused by Gemfibrozil mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[15]
Fenofibrate	DMFKXDY	Moderate	Decreased metabolism of Montelukast caused by Fenofibrate mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[15]
Teriflunomide	DMQ2FKJ	Moderate	Decreased metabolism of Montelukast caused by Teriflunomide mediated inhibition of CYP450 enzyme.	Hyper-lipoproteinaemia [5C80]	[15]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Montelukast caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[16]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Montelukast caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[15]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Montelukast caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[22]
Vemurafenib	DM62UG5	Moderate	Decreased metabolism of Montelukast caused by Vemurafenib mediated inhibition of CYP450 enzyme.	Melanoma [2C30]	[15]
Dabrafenib	DMX6OE3	Moderate	Increased metabolism of Montelukast caused by Dabrafenib mediated induction of CYP450 enzyme.	Melanoma [2C30]	[16]
Exjade	DMHPRWG	Moderate	Decreased metabolism of Montelukast caused by Exjade mediated inhibition of CYP450 enzyme.	Mineral absorption/transport disorder [5C64]	[15]
Rifabutin	DM1YBHK	Moderate	Increased metabolism of Montelukast caused by Rifabutin mediated induction of CYP450 enzyme.	Mycobacterium infection [1B10-1B21]	[16]
Imatinib	DM7RJXL	Moderate	Decreased metabolism of Montelukast caused by Imatinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[15]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Montelukast caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[15]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Montelukast caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[23]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Montelukast caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[24]
ABIRATERONE	DM8V75C	Moderate	Decreased metabolism of Montelukast caused by ABIRATERONE mediated inhibition of CYP450 enzyme.	Prostate cancer [2C82]	[15]
Enzalutamide	DMGL19D	Moderate	Increased metabolism of Montelukast caused by Enzalutamide mediated induction of CYP450 enzyme.	Prostate cancer [2C82]	[16]
Bosentan	DMIOGBU	Moderate	Increased metabolism of Montelukast caused by Bosentan mediated induction of CYP450 enzyme.	Pulmonary hypertension [BB01]	[16]
Dexamethasone	DMMWZET	Moderate	Increased metabolism of Montelukast caused by Dexamethasone mediated induction of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[16]
Nafcillin	DMN9RPO	Moderate	Increased metabolism of Montelukast caused by Nafcillin mediated induction of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[16]
Leflunomide	DMR8ONJ	Moderate	Decreased metabolism of Montelukast caused by Leflunomide mediated inhibition of CYP450 enzyme.	Rheumatoid arthritis [FA20]	[15]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Montelukast caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[25]
Sulfamethizole	DMGCHDS	Moderate	Decreased metabolism of Montelukast caused by Sulfamethizole mediated inhibition of CYP450 enzyme.	Urinary tract infection [GC08]	[15]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Montelukast caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[16]
Amiodarone	DMUTEX3	Moderate	Decreased metabolism of Montelukast caused by Amiodarone mediated inhibition of CYP450 enzyme.	Ventricular tachyarrhythmia [BC71]	[15]
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⏷ Show the Full List of 56 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Aspartame	E00402	134601	Flavoring agent
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
FD&C blue no. 2	E00446	2723854	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Lactic acid	E00020	612	Acidulant
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium stearyl fumarate	E00545	23665634	lubricant
Sucralose	E00370	71485	Flavoring agent
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butylhydroxyanisole	E00308	24667	Antimicrobial preservative; Antioxidant
Carmellose sodium	E00625	Not Available	Disintegrant
Dextrin	E00359	62698	Binding agent; Diluent; Microencapsulating agent; Stiffening agent; Suspending agent; Viscosity-controlling agent
Edetate disodium	E00186	8759	Complexing agent
Eisenoxyd	E00585	56841934	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
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⏷ Show the Full List of 32 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Montelukast 4 mg tablet	4 mg	Chewable Tablet	Oral
Montelukast 5 mg tablet	5 mg	Chewable Tablet	Oral
Montelukast 10 mg tablet	10 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Montelukast FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3340).
3	The COvid-19 Symptom MOntelukast Trial (COSMO)
4	BDDCS applied to over 900 drugs
5	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
6	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8	Protective potential of montelukast against hepatic ischemia/reperfusion injury in rats. J Surg Res. 2010 Mar;159(1):588-94.
9	As a potential treatment of COVID-19: Montelukast. Med Hypotheses. 2020 May 11;142:109828.
10	Effects of polymorphisms of the SLCO2B1 transporter gene on the pharmacokinetics of montelukast in humans. J Clin Pharmacol. 2013 Nov;53(11):1186-93.
11	Effect of citrus juice and SLCO2B1 genotype on the pharmacokinetics of montelukast. J Clin Pharmacol. 2011 May;51(5):751-60.
12	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
13	In vitro metabolism of montelukast by cytochrome P450s and UDP-glucuronosyltransferases. Drug Metab Dispos. 2015 Dec;43(12):1905-16.
14	Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem. 2008 Jun 20;283(25):17227-37.
15	Karonen T, Filppula A, Laitila J, Niemi M, Neuvonen PJ, Backman JT "Gemfibrozil Markedly Increases the Plasma Concentrations of Montelukast: A Previously Unrecognized Role for CYP2C8 in the Metabolism of Montelukast." Clin Pharmacol Ther (2010):. [PMID: 20592724]
16	Product Information. Singulair (montelukast). Merck & Co, Inc, West Point, PA.
17	Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA.
18	Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ.
19	Product Information. Korlym (mifepristone). Corcept Therapeutics Incorporated, Menlo Park, CA.
20	Cerner Multum, Inc. "Canadian Product Information.".
21	Jerntorp P, Almer LO "Chlorpropamide-alcohol flushing in relation to macroangiopathy and peripheral neuropathy in non-insulin dependent diabetes." Acta Med Scand 656 (1981): 33-6. [PMID: 6953748]
22	Product Information. Copiktra (duvelisib). Verastem, Inc., Needham, MA.
23	Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
24	Product Information. Fycompa (perampanel). Eisai Inc, Teaneck, NJ.
25	Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.